Sodium Hydroxide → HCID 67234564, compound

HRID 2368726Notes

Reaction equation

HRID 2368726 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[S:4][C:3]=1[CH:14]=[O:15].[OH-:16].[Na+]>[N+]([O-])([O-])=O.[Ag+].C(O)C>[CH3:1][C:2]1[CH:6]=[C:5]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[S:4][C:3]=1[C:14]([OH:16])=[O:15]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86607510HCID 86607510, compound

Product 1

HCID 67234564HCID 67234564, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 702EthanolSolvent

Procedure

3-Methyl-5-phenoxy-thiophene-2-carbaldehyde, (example 22.a, 5.68 g, 25.9 mmol) was added to 26 mL of ethanol. To the mixture were added 21 mL of 5 N NaOH(aq) and silver nitrate (8.81 g, 52 mmol), and the resultant mixture was stirred for 19 hours at room temperature. The mixture was filtered through a pad of celite, washing the solid with ca. 50-100 mL portions of 1 N NaOH solution three times. The basic solution was washed with ethyl ether, then acidified with concentrated H2SO4, and extracted twice with ethyl acetate. The organic fractions were dried over anhydrous sodium sulfate and concentrated under high vacuum to 5.7 g of a yellow solid: MS: (−) m/z 232.9 (M−1)

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. washwashing the solid with ca. 50-100 mL portions of 1 N NaOH solution three times
  3. washThe basic solution was washed with ethyl ether
  4. extractionextracted twice with ethyl acetate
  5. dry with materialThe organic fractions were dried over anhydrous sodium sulfate
  6. concentrationconcentrated under high vacuum to 5.7 g of a yellow solid

Sources & evidence

ORD record
ord-1ed36f191d244c898d437e76d4292e89
Source dataset
uspto-grants-2014_04
Patent number
US08703795B2

Reaction notes

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